This essay outlines a course for U.S. legal historical writing distinct from the ascendant mode of the last thirty years, generally known as “critical legal history” or “critical historicism.” Critical legal history is premised on the conventional historical strategy of exploring the nature of an object by situating it in an appropriate context and examining the conjunction between object and context. In CLH’s case the object is law and the context is polity, economy, or society, or more usually a realm of action that is a mixture of all three. CLH is also premised on the further, theoretical, contention that whatever the realm of action in relation to which law is situated, the outcome is the same: indeterminacy marked by contingency, alternative possibilities, “paths not taken.” In this regard, CLH shares in the general turn in the qualitative social sciences and humanities toward “complexity.” The results of this contextualizing or relational approach have been empirically rich but are inevitably marked by an abandonment of authoritative causal explanation (metatheory) for thick description. This essay lays out an alternative to CLH’s parsing of relations between law and what is extrinsic to it, by exploring the explanatory potential of allegory, by which what are imagined as distinct become the same. Allegory is strikingly “visual” in conception – figurative, emblematic. Wycliffe called it “ghostly understanding.” I explore the potential of allegory along three optical dimensions – scope (appearance), scale (perspective), and structure (constellation) – that together produce what Walter Benjamin called “the dialectical image,” a non-relational theory of representation with striking historical applications.